Thoroughbreds are, at times, difficult to understand. It’s up to their trainers and owners to find ways to help them win races.

Whirlaway was an elongated chestnut under the tutelage of trainer Ben A. Jones at illustrious Calumet Farm in 1941. Jones and jockey Eddie Arcaro were convinced that Whirlaway was very much a creature of habit. In his races, he developed an inclination to run anything but a straight line. He would invariably move to his right in the stretch, causing problems with interference and getting too much attention from the stewards.

Jones fitted Whirlaway with blinkers that had only one cup covering his right eye. A tiny, almost imperceptible hole was cut in the covering. After that, Whirlaway ran straight ahead and ended up winning the 1941 Triple Crown. When he posted a victory in the Travers that year, he became the lone thoroughbred in history to win the Triple Crown and the Travers.

A robust chestnut with a long, flowing tail, Whirlaway appeared to be almost an elongated streak of a running Pegasus when going at full throttle. So handsome was he that he was called “Mr. Longtail,” with his thick, reddish tail nearly straight-out in full sail behind him.

He was sired by the English Derby champion, Blenheim. Calumet Farm was sure he could be a champion and when he appeared misguided when running, it left no stone uncovered in trying to rectify his off-line directions.

The farm with the famous red-trimmed roofs on its barns and stables was proved to be correct on its early estimations of Whirlaway’s potential for greatness. He won the Kentucky Derby by a standing-record eight lengths.

And then came wins in both the Preakness and Belmont Stakes. Later, in August 1941, he won the so-called “Midsummer Classic” – the Travers Stakes at Saratoga.

When racing in 1942, it was George “The Iceman” Woolf doing the riding because Arcaro had been suspended due to on-track infractions.

When finally retired from racing, “Mr. Longtail” had raced 60 times – winning 32, finishing second another 15 times and coming in third another nine times.

For a “quirky” thoroughbred with negative habits that needed correcting, he was still one of the most successful runners in the first half of the 20th century.

Whirlaway was voted into the Racing Museum and Hall of Fame in 1959.

Arcaro, who rode other Calumet Farm greats like Citation and Coaltown, often was questioned about the comparitive features of “Mr. Longtail” and Citation, another Triple Crown champion. The Hall of Fame rider said the two champions were nearly equal with the only real differences being Whirlaway’s unusual traits and Citation’s more composed behavior that made him easier to understand and rate during races.

The racing public had affection for both champions and found it easier to follow the running of Whirlaway on the backstretch because of his long, flowing tail.

Thoroughbred racing was king in the early 1940s, and the public was glad to place Whirlaway on his throne with his Triple Crown and Travers laurels.